The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Cyclopentenyl     cyclopentene

Synonyms: AC1L3EGQ, 10577-65-8, 14461-09-7, 2-cyclopentenyl, 4-cyclopentenyl, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of cyclopentene


High impact information on cyclopentene


Chemical compound and disease context of cyclopentene


Biological context of cyclopentene


Anatomical context of cyclopentene


Associations of cyclopentene with other chemical compounds

  • Several cyclopentene GABA analogues were synthesized as conformationally rigid analogues of the epilepsy drug vigabatrin and tested as inhibitors and substrates of gamma-aminobutyric acid aminotransferase (GABA-AT) [19].
  • W(CO)5(L)-catalyzed endo-selective cyclization of allenyl silyl enol ethers: an efficient method for the cyclopentene annulation onto alpha,beta-unsaturated ketones [20].
  • The effects of the cyclopentenyl (cCyd) and cyclopentyl (carbodine) analogues of cytidine on differentiation, and nucleic acid and nucleotide biosynthesis, were examined in the human promyelocytic leukemia cell line HL-60 [21].
  • Indene and cyclopentene enaminonitriles were reacted with SCl2, iBu3N and NCS to give the first cyclopenta[1,2,6]thiadiazines that showed unusual characteristics, one as a NIR dye and another as a liquid crystal [22].
  • In silico screening of pyrimidine-nucleoside analogs has revealed a number of potential lead compounds that, if bound to Mtb pyrR, could facilitate transcriptional attenuation, particularly cyclopentenyl nucleosides [23].

Gene context of cyclopentene

  • A previously discovered DHODH inhibitor series was further improved by replacing the cyclopentene ring by aromatic heterocycles [24].
  • A direct SN2 displacement on the cyclopentenyl mesylate 3 by the sodium salt of 6-chloro-3-deazapurine afforded the desired regioisomer 4 as the major product [25].
  • SN2 reaction of the known cyclopentenyl units 12 and 13 with 2-haloadenines under basic conditions gave the protected carbocyclic nucleosides 14b,c and 15b,c, respectively [26].
  • This cycloadduct ring opening methodology was applied to the synthesis of a unique cyclopentenyl hydroxamic acid-based inhibitor of 5-lipoxygenase [27].
  • The deamination of CPE-C to cyclopentenyl uridine by cytidine deaminase was investigated with the purified enzyme from human placenta [28].

Analytical, diagnostic and therapeutic context of cyclopentene


  1. Reversal by vitamin A analogues (retinoids) of hyperplasia induced by N-methyl-N'-nitro-N-nitrosoguanidine in mouse prostate organ cultures. Chopra, D.P., Wilkoff, L.J. J. Natl. Cancer Inst. (1977) [Pubmed]
  2. Antitumor activity and biochemical effects of cyclopentenyl cytosine in mice. Moyer, J.D., Malinowski, N.M., Treanor, S.P., Marquez, V.E. Cancer Res. (1986) [Pubmed]
  3. In situ cyclopentenyl cytosine infusion for the treatment of experimental brain tumors. Viola, J.J., Agbaria, R., Walbridge, S., Oshiro, E.M., Johns, D.G., Kelley, J.A., Oldfield, E.H., Ram, Z. Cancer Res. (1995) [Pubmed]
  4. Evaluation of vitamin A analogs in modulating epithelial differentiation of 13-day chick embryo metatarsal skin explants. Wilkoff, L.J., Peckham, J.C., Dulmadge, E.A., Mowry, R.W., Chopra, D.P. Cancer Res. (1976) [Pubmed]
  5. A bacteriorhodopsin analog reconstituted with a nonisomerizable 13-trans retinal derivative displays light insensitivity. Bhattacharya, S., Marti, T., Otto, H., Heyn, M.P., Khorana, H.G. J. Biol. Chem. (1992) [Pubmed]
  6. Novel 6,5-fused ring heterocyclic antifolates: biochemical and biological characterization. McGuire, J.J., Bergoltz, V.V., Heitzman, K.J., Haile, W.H., Russell, C.A., Bolanowska, W.E., Kotake, Y., Haneda, T., Nomura, H. Cancer Res. (1994) [Pubmed]
  7. Pharmacokinetics and metabolism of cyclopentenyl cytosine in nonhuman primates. Blaney, S.M., Balis, F.M., Hegedus, L., Heideman, R.L., McCully, C., Murphy, R.F., Kelley, J.A., Poplack, D.G. Cancer Res. (1990) [Pubmed]
  8. A retinoic acid-binding protein from chick embryo skin. Sani, B.P., Hill, D.L. Cancer Res. (1976) [Pubmed]
  9. A single point mutation in CTP synthetase of Chlamydia trachomatis confers resistance to cyclopentenyl cytosine. Wylie, J.L., Wang, L.L., Tipples, G., McClarty, G. J. Biol. Chem. (1996) [Pubmed]
  10. Gold-Catalyzed Deoxygenated Cyclization of cis-2,4-Dien-1-als with Regioselective Addition of Two Nucleophiles. One-Pot Synthesis of Highly Functionalized Cyclopentene Framework. Lin, C.C., Teng, T.M., Odedra, A., Liu, R.S. J. Am. Chem. Soc. (2007) [Pubmed]
  11. Chaulmoogric acid: assimilation into the complex lipids of mycobacteria. Cabot, M.C., Goucher, C.R. Lipids (1981) [Pubmed]
  12. Diastereoisomeric cationic pi-allylpalladium-(P,C)-MAP and MOP complexes and their relationship to streochemical memory effects in allylic alkylation. Lloyd-Jones, G.C., Stephen, S.C., Murray, M., Butts, C.P., Vyskocil, S., Kocovský, P. Chemistry (Weinheim an der Bergstrasse, Germany) (2000) [Pubmed]
  13. 1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity. Daluge, S.M., Good, S.S., Faletto, M.B., Miller, W.H., St Clair, M.H., Boone, L.R., Tisdale, M., Parry, N.R., Reardon, J.E., Dornsife, R.E., Averett, D.R., Krenitsky, T.A. Antimicrob. Agents Chemother. (1997) [Pubmed]
  14. Short total synthesis of (+)-madindolines A and B. Hirose, T., Sunazuka, T., Shirahata, T., Yamamoto, D., Harigaya, Y., Kuwajima, I., Omura, S. Org. Lett. (2002) [Pubmed]
  15. Phase I clinical trial of continuous infusion cyclopentenyl cytosine. Politi, P.M., Xie, F., Dahut, W., Ford, H., Kelley, J.A., Bastian, A., Setser, A., Allegra, C.J., Chen, A.P., Hamilton, J.M. Cancer Chemother. Pharmacol. (1995) [Pubmed]
  16. Structural features resulting in convulsive activity of carbapenem compounds: effect of C-2 side chain. Sunagawa, M., Matsumura, H., Sumita, Y., Nouda, H. J. Antibiot. (1995) [Pubmed]
  17. Cyclopentenyl cytidine analogue. An inhibitor of cytidine triphosphate synthesis in human colon carcinoma cells. Glazer, R.I., Knode, M.C., Lim, M.I., Marquez, V.E. Biochem. Pharmacol. (1985) [Pubmed]
  18. The direct mutagenicity of aflatoxin B1 and metabolites to Salmonella typhimurium: structure mutagenicity relationships and mechanisms of action. Yourtee, D.M., Kirk-Yourtee, C.L., Searles, S. Res. Commun. Chem. Pathol. Pharmacol. (1987) [Pubmed]
  19. Inhibition and substrate activity of conformationally rigid vigabatrin analogues with gamma-aminobutyric acid aminotransferase. Qiu, J., Pingsterhaus, J.M., Silverman, R.B. J. Med. Chem. (1999) [Pubmed]
  20. W(CO)5(L)-catalyzed endo-selective cyclization of allenyl silyl enol ethers: an efficient method for the cyclopentene annulation onto alpha,beta-unsaturated ketones. Miura, T., Kiyota, K., Kusama, H., Lee, K., Kim, H., Kim, S., Lee, P.H., Iwasawa, N. Org. Lett. (2003) [Pubmed]
  21. Induction of differentiation in the human promyelocytic leukemia cell line HL-60 by the cyclopentenyl analogue of cytidine. Glazer, R.I., Cohen, M.B., Hartman, K.D., Knode, M.C., Lim, M.I., Marquez, V.E. Biochem. Pharmacol. (1986) [Pubmed]
  22. Cyclopentathiadiazines, new heterocyclic materials from cyclic enaminonitriles. Macho, S., Miguel, D., Neo, A.G., Rodriguez, T., Torroba, T. Chem. Commun. (Camb.) (2005) [Pubmed]
  23. Structure of pyrR (Rv1379) from Mycobacterium tuberculosis: a persistence gene and protein drug target. Kantardjieff, K.A., Vasquez, C., Castro, P., Warfel, N.M., Rho, B.S., Lekin, T., Kim, C.Y., Segelke, B.W., Terwilliger, T.C., Rupp, B. Acta Crystallogr. D Biol. Crystallogr. (2005) [Pubmed]
  24. Biphenyl-4-ylcarbamoyl thiophene carboxylic acids as potent DHODH inhibitors. Leban, J., Kralik, M., Mies, J., Baumgartner, R., Gassen, M., Tasler, S. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  25. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities. Tseng, C.K., Marquez, V.E., Fuller, R.W., Goldstein, B.M., Haines, D.R., McPherson, H., Parsons, J.L., Shannon, W.M., Arnett, G., Hollingshead, M. J. Med. Chem. (1989) [Pubmed]
  26. New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A. Obara, T., Shuto, S., Saito, Y., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E., Matsuda, A. J. Med. Chem. (1996) [Pubmed]
  27. Regio- and stereoselective ring openings of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene systems with copper catalyst-modified grignard reagents: application to the synthesis of an inhibitor of 5-lipoxygenase. Surman, M.D., Mulvihill, M.J., Miller, M.J. J. Org. Chem. (2002) [Pubmed]
  28. Enhancement of the antileukemic activity of 5-aza-2'-deoxycytidine by cyclopentenyl cytosine in HL-60 leukemic cells. Bouffard, D.Y., Momparler, L.F., Momparler, R.L. Anticancer Drugs (1994) [Pubmed]
  29. Measurement of cyclopentenyl cytosine 5'-triphosphate in vitro and in vivo by multidimensional high-performance liquid chromatography. Agbaria, R., Ford, H., Kelley, J.A., Xie, F., Politi, P., Grem, J.L., Cooney, D.A., Marquez, V.E., Allegra, C.J., Johns, D.G. Anal. Biochem. (1993) [Pubmed]
WikiGenes - Universities